[2-[(8S,9S,10R,11R,13S,14S,17R)-11,17-二羟基-10,13-二甲基-3-氧代-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊并[a]菲-17-基]-2-氧代-乙基](2S,3S,4S,5R)-2,3,4,5-四羟基-6-氧代-己酸酯 | 7301-54-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: [2-[(8S,9S,10R,11R,13S,14S,17R)-11,17-二羟基-10,13-二甲基-3-氧代-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊并[a]菲-17-基]-2-氧代-乙基](2S,3S,4S,5R)-2,3,4,5-四羟基-6-氧代-己酸酯
• 英文名称: cortisol 21-glucuronide
• 英文别名: pregn-4-en-11β,17α,21-triol-3,20-dione-21-O-glucuronide；[2-[(8S,9S,10R,11R,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxo-hexanoate；(2S,3S,4S,5R,6R)-6-[2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 7301-54-4
• 化学式: C₂₇H₃₈O₁₁
• 分子量: 538.592
• InChiKey: SXDBDFVHISOKJP-YXSMBZLISA-N

物化性质

• 熔点：
  160-162 °C
• 沸点：
  818.3±65.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  191
• 氢给体数：
  6
• 氢受体数：
  11

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  氢化可的松	HYDROCORTISONE	50-23-7	C21H30O5	362.466

反应信息

• 作为产物：
  描述：

  pregn-4-en-11β,17α,21-triol-3,20-dione-21-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronate) 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80%的产率得到[2-[(8S,9S,10R,11R,13S,14S,17R)-11,17-二羟基-10,13-二甲基-3-氧代-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊并[a]菲-17-基]-2-氧代-乙基](2S,3S,4S,5R)-2,3,4,5-四羟基-6-氧代-己酸酯
  参考文献：
  名称：

  Corticosteroids 21-glucuronides: Synthesis and complete characterization by 1H and 13C NMR

  摘要：

  Despite the important physiological role of the corticosteroids glucuronides, very poor NMR data for this class of compounds are reported. For this reason we prepared a set of corticosteroids and submitted them to a detailed NMR study. A complete assignment of H-1 and C-13 signals was accomplished arranging mono- and two-dimensional NMR techniques. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.06.003

文献信息

• Enzyme-assisted synthesis and characterization of glucuronide conjugates of neuroactive steroids
  作者：Sirkku E. Jäntti、Alexandros Kiriazis、Ruut R. Reinilä、Risto K. Kostiainen、Raimo A. Ketola

  DOI：10.1016/j.steroids.2006.11.023

  日期：2007.3

  Synthesis of reference standards is needed to determine the presence and function of steroid glucuronides in the brain or other tissues, because commercial sources of steroid glucuronide standards are limited or unavailable. In the present study porcine, rat, and bovine liver microsomes were tested to evaluate their ability to glucuronidate eight neurosteroids and neuroactive steroids of various types: dehydroepiandrosterone, pregnenolone, iso-pregnanolone, 5 alpha-tetrahydrodeoxycorticosterone, corticosterone, cortisol, P-estradiol, and testosterone. In general, the glucuronidation efficiency of rat liver was rather poor compared with that of bovine and porcine liver microsomes. Since porcine liver apparently has a relatively large amount of dehydrogenase, its microsomes also produced dehydrogenated steroids and their glucuronides, as well as various regioisomers in which the site of glucuronidation varied. In contrast, bovine liver microsomes produced mainly a single major glucuronidation product and few dehydrogenation products and gave the best overall yield for two-third of the steroids tested. The enzymatic synthesis of five glucuronides of four steroids was carried out and the conditions, purification, and analytical methods for the glucuronidation products were optimized. The steroid glucuronides synthesized were characterized by nuclear magnetic resonance spectroscopy (NMR) and liquid chromatography-mass spectrometry (LC-MS). The stereochemically pure steroid glucuronide conjugates were recovered in milligram amounts (yield 10-78%) and good purity (> 85-90%), which is sufficient for LC-MS/MS method development and analyses of steroid glucuronicles in biological matrices such as brain, urine, or plasma. (c) 2006 Elsevier Inc. All rights reserved.
• Corticosteroids 21-glucuronides: Synthesis and complete characterization by 1H and 13C NMR
  作者：Pierangela Ciuffreda、Silvana Casati、Maria De Mieri、Patrizia Ferraboschi

  DOI：10.1016/j.steroids.2009.06.003

  日期：2009.10

  Despite the important physiological role of the corticosteroids glucuronides, very poor NMR data for this class of compounds are reported. For this reason we prepared a set of corticosteroids and submitted them to a detailed NMR study. A complete assignment of H-1 and C-13 signals was accomplished arranging mono- and two-dimensional NMR techniques. (C) 2009 Elsevier Inc. All rights reserved.